Find short term rentals in Chesapeake, VA at the best prices

790 available short term rental offers

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Chesapeake, VA short term rentals
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Best Short term and Weekly rentals in Chesapeake, VA

Best Chesapeake, VA luxury short term rentals

Your Home Away From Home And Near Va Beach - Chesapeake, VA
8.8 12 reviews

Your Home Away From Home And Near Va Beach

apartment, Portsmouth
This four-bedroom Portsmouth house, sleeping up to ten guests, is situated in a quiet neighbourhood, approximately 24km from Portsmouth Naval Hospital and 40km from Virginia Beach.
The property boasts a spacious interior with a large living room, dining room, office, fully equipped kitchen including dishwasher, two bathrooms (one with Jacuzzi), Wi-Fi, Roku TVs, and private gardens with parking; ideal for families or groups visiting the area's military bases.

Best Chesapeake, VA Short term rentals with a jacuzzi

Among the 790 accommodations in Chesapeake, VA, here are the 4 best rentals with a jacuzzi

Spacious 4br-corporate/military & Medical Stay - Chesapeake, VA
No reviews

Spacious 4br-corporate/military & Medical Stay

apartment, Suffolk
This fully furnished 4-bedroom house in Suffolk offers convenient access to local amenities for extended stays.
This residence includes air conditioning, a kitchen with a fridge, Wi-Fi, and parking, accommodating up to 6 guests with a garden and jacuzzi for comfortable living.
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great For Business Travelers! - Chesapeake, VA
No reviews

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great For Business Travelers!

apartment, Chesapeake
This Chesapeake, Virginia aparthotel offers a convenient location, a 9-minute walk from the Chesapeake Conference Centre and a 1.8km drive from Greenbrier Mall, with easy beach access.
The self-catering apartment features a fully equipped kitchen, one bedroom, one bathroom, sleeps two guests, and includes a swimming pool, jacuzzi, and on-site parking.
The Manor- Extended Stays - Chesapeake, VA
10 8 reviews

The Manor- Extended Stays

apartment, Chesapeake
This Chesapeake apartment, near Greenbrier Mall, offers easy access to the Oceanfront, Norfolk Waterside, and Norfolk Outlets.
The four-bedroom, two-bathroom property sleeps eight, features a recently remodelled kitchen with modern appliances, a 65-inch TV, free Wi-Fi, and self check-in; nearby attractions include the Chesapeake Jubilee and Deep Creek Locks.
Free Breakfast. Indoor Pool & Hot Tub. Close To The Virginia Beach Business District! - Chesapeake, VA
8.0 5 reviews

Free Breakfast. Indoor Pool & Hot Tub. Close To The Virginia Beach Business District!

apartment, Chesapeake
This Chesapeake City seaside apartment is situated 0.8km from the Chesapeake Conference Centre, 4.8km from Greenbrier Mall, and 4.8km from Chesapeake City Park.
This one-bedroom, one-bathroom flat sleeps six guests and boasts an indoor pool, hot tub, complimentary breakfast, and a fully equipped kitchen including a fridge, microwave, and dishwasher; free Wi-Fi and limited housekeeping are also provided.

Frequently Asked Questions about short term rentals in Chesapeake, VA

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Best family friendly Chesapeake, VA Short term rentals

Among the 790 accommodations in Chesapeake, VA, here are the 4 best family friendly rentals

Sojourn 2 Bedroom Townhouse In Virginia Beach - Chesapeake, VA
9.3 29 reviews

Sojourn 2 Bedroom Townhouse In Virginia Beach

apartment, Virginia Beach
This apartment is located just a few kilometres from the bustling heart of Virginia Beach, offering easy access to shops, restaurants and the beach. It has been rated very good for cleanliness and user experience, and excellent for location.
The apartment has two bedrooms and one bathroom, comfortably sleeping up to five guests. It comes equipped with a well-stocked kitchen, comfortable living space, and access to streaming services, ensuring a relaxing and enjoyable stay.
The Chesapeake Gray  Historical Waterside District 20 Mins To Oceanfront - Chesapeake, VA
9.4 8 reviews

The Chesapeake Gray Historical Waterside District 20 Mins To Oceanfront

apartment, Norfolk
This Norfolk apartment is located within easy reach of both Waterside Festival Marketplace and Virginia Beach Town Center, offering a convenient base for exploring the city and its surroundings. The apartment is just a short drive from the beach, providing a perfect blend of urban convenience and coastal charm.
The property is a spacious three-bedroom home that comfortably sleeps six guests. It offers a modern kitchen, a private backyard with a patio, and a jacuzzi, ideal for relaxing after a day of exploring the local attractions.
Portsmouth 3br Near Casino | Spacious Yard Stay - Chesapeake, VA
9.5 66 reviews

Portsmouth 3br Near Casino | Spacious Yard Stay

apartment, Portsmouth
This Portsmouth house is ideally situated just a short drive from the new Rivers Casino and within easy reach of downtown Portsmouth, Norfolk, Virginia Beach, and Chesapeake. The accommodation has received excellent ratings for cleanliness and location, and is rated very good overall.
The house has 3 bedrooms and 2 bathrooms, comfortably sleeping 6 guests. It features modern amenities like a kitchen with a fridge and microwave, a washer and dryer, high-speed Wi-Fi, multiple TVs with streaming services, a large fenced backyard with a patio, furniture, and a gas grill, and security features like exterior cameras and an ADT security system.
Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8 - Chesapeake, VA
9.2 7 reviews

Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8

apartment, Portsmouth
This holiday home is located in Portsmouth, just 1.5 km from Rivers Casino Portsmouth, and within 10 km of Portsmouth City Park and Frank D Lawrence Stadium. It has consistently received excellent user ratings, making it a popular choice for travellers.
The property offers 93 square metres of space and can comfortably accommodate up to 6 guests in its 3 bedrooms. The kitchen comes equipped with a fridge, microwave, oven, and dishwasher, while the garden provides a relaxing outdoor space. Guests can also enjoy free Wi-Fi, air conditioning, a terrace, and parking.

Best Chesapeake, VA lodging with parking

Cozy Cute Apartment - Chesapeake, VA
9.8 39 reviews

Cozy Cute Apartment

apartment, Portsmouth
This one-bedroom flat in Portsmouth is centrally located, offering immediate access to Old Town Portsmouth's dining and entertainment, and is just 600 meters from City Park.
This pet-friendly apartment accommodates two guests, features air conditioning and parking, and is conveniently situated for day trips to Norfolk beaches (32 kilometres away) and attractions like Oceanfront and Busch Gardens (64 kilometres away).
Beautiful, Modern Furnished 3-bedroom, 2-bathroom Cottage Near Attractions. - Chesapeake, VA
10 13 reviews

Beautiful, Modern Furnished 3-bedroom, 2-bathroom Cottage Near Attractions.

apartment, Portsmouth
This Portsmouth cottage, situated 3.5km from Bon Secours Maryview Medical Center and 7.6km from Portsmouth Naval Hospital, offers easy access to major roads, shopping centres, and restaurants.
The 111 square metre property comprises three bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen with appliances such as an Instant Pot and air fryer, plus on-site parking and in-unit laundry facilities.
R & R River House - Chesapeake, VA
9.9 97 reviews

R & R River House

apartment, Portsmouth
This luxurious Portsmouth apartment boasts stunning water views and is conveniently located approximately 1.6km from a city park, 7.2km from a casino, and 11km from Portsmouth city centre.
The two-bedroom, one-bathroom property sleeps six guests and features a fully equipped kitchen with fridge, microwave, and dishwasher, air conditioning, a garden, parking, and a master bedroom with a private balcony; explore nearby attractions including Waterside, 12km away, and Virginia Beach, 40km away.
Hidden Gem A Comfortable 4bedroom Home With A Fenced-in Yard. - Chesapeake, VA
10 10 reviews

Hidden Gem A Comfortable 4bedroom Home With A Fenced-in Yard.

apartment, Portsmouth
This Portsmouth holiday home is situated within 5km of Portsmouth City Park, Chesapeake Square Mall, and Rivers Casino Portsmouth, offering easy access to local amenities and attractions.
The 160 square metre property boasts four bedrooms, two bathrooms, sleeping up to eight guests, and features a fully equipped kitchen, garden, patio, free Wi-Fi, and parking.
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